Phenylhydrazine → HCID 70451592, compound

HRID 1285304Notes

Reaction equation

HRID 1285304 reaction equation
[CH2:1]([N:4]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=O)[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].[C:16]1([NH:22][NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO>[C:16]1([NH:22][N:23]=[CH:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[N:4]([CH2:5][CH:6]=[CH2:7])[CH2:1][CH:2]=[CH2:3])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 19350314HCID 19350314, compound

Product 1

HCID 70451592HCID 70451592, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1 mole of N,N-diallylaminobenzaldehyde in methanol, was added 1.2 moles of phenylhydrazine. The mixture was heated under reflux for about 2 hours to yield diallylaminobenzaldehyde N-phenylhydrazone (melting point: 63.5°-65.0° C.). Into a mixture of 5 cc of 5N sodium hydroxide solution and 20 cc of dimethyl sulfoxide, were added 5.0 g of said hydrazone and 4.8 g of allyl bromide. The mixture was stirred for 2 hours at room temperature. After completion of the reaction, 50 cc of water and ethyl acetate were added to the reaction mixture to extract the organic layer. The extract was freed from the ethyl acetate by distillation and the residue was recrystallized from 150 cc of alcohol to yield 3.8 g of pale yellowish white crystals melting at 38.5°-40.0° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for about 2 hours

Sources & evidence

ORD record
ord-8b9a8858526e4295b8e3e6d5bf9a7a50
Source dataset
uspto-grants-1986_01
Patent number
US04567126

Reaction notes

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